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On the IUPAC nomenclature of ethers and esters

  1. Feb 8, 2014 #1

    I was wondering if there is a systematic procedure to follow when naming complex organic molecules containing ethers and esters. By "complex" I mean organic molecules that contain multiple ether/ester groups and possibly within multiple different branches of the molecule.

    1.How to determine the alkoxy/alkyl groups when there are multiple ether linkages in the molecule?
    E.g. CH2---O---CH2CH3CH2---O---CH3CH2CH2---O---CH2

    -Similarly, how to name the alkyl group when there are multiple ester groups in the molecule?
    E.g. CH3---COO---CH2CH3CH2---COO---CH3

    2.How to name the alkoxy group when it contains an aldehyde or carboxylic acid?
    E.g. COOH---CH2---O---CH2---COOH
    I'm guessing that I'd have to switch to prefix notation, so the compound above would be called
    "2-carboxymethoxyethanoic acid" or "dicarboxymethyl ether"?

    If that is the case, how would you name the ether if the carboxyl/oxo group is directly attached to the Oxygen, like this:
    COOH --O -- COOH or CHO --O --CHO ?

    3. How do you name aldehydes/carboxylic acids joined by an ester?
    E.g. CHO---CH2---COO---CH2---COOH
    So now do I have to switch to prefix form for both groups? Thus, would this molecule be named
    "carboxylmethyl 3-oxopropanoate"?

    My textbook and most sources on the internet only covers the simple stuff. Please help me.
    (I apologize for the messy diagrams but there is no LaTex symbols for organic chemistry)

    Attached Files:

    Last edited: Feb 8, 2014
  2. jcsd
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